Asymmetric Friedel-Crafts alkylation of indoles with nitrodienes and 2-propargyloxy-β-nitrostyrenes catalyzed by diphenylamine-linked bis(oxazoline)-Zn(OTf) 2 complexes

Jiahuan Peng; Da Ming Du

doi:10.1002/ejoc.201200382

Asymmetric Friedel-Crafts alkylation of indoles with nitrodienes and 2-propargyloxy-β-nitrostyrenes catalyzed by diphenylamine-linked bis(oxazoline)-Zn(OTf) ₂ complexes

Jiahuan Peng
, Da Ming Du^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Beijing Institute of Technology

Research output: Contribution to journal › Article › peer-review

41 Citations (Scopus)

Abstract

The catalytic asymmetric Friedel-Crafts reaction of indoles with nitrodienes and 2-propargyloxy-β-nitrostyrenes was systematically investigated with diphenylamine-linked bis(oxazoline)-Zn(OTf) ₂ complexes. Moderate to good enantioselectivities were obtained with both kinds of substrates (up to 89 % ee for nitrodienes and up to 93 % ee for β-nitrostyrene derivatives). Further transformation of the corresponding Friedel-Crafts alkylation product of indole with 2-propargyloxy-β- nitrostyrene was carried out to give the chiral isoxazolobenzoxepane derivative, which is of medicinal chemistry interest, with retained enantiomeric purity.

Original language	English
Pages (from-to)	4042-4051
Number of pages	10
Journal	European Journal of Organic Chemistry
Issue number	21
DOIs	https://doi.org/10.1002/ejoc.201200382
Publication status	Published - Jul 2012

Keywords

Alkenes
Alkylation
Asymmetric catalysis
Nitrogen heterocycles
Synthetic methods

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title = "Asymmetric Friedel-Crafts alkylation of indoles with nitrodienes and 2-propargyloxy-β-nitrostyrenes catalyzed by diphenylamine-linked bis(oxazoline)-Zn(OTf) 2 complexes",

abstract = "The catalytic asymmetric Friedel-Crafts reaction of indoles with nitrodienes and 2-propargyloxy-β-nitrostyrenes was systematically investigated with diphenylamine-linked bis(oxazoline)-Zn(OTf) 2 complexes. Moderate to good enantioselectivities were obtained with both kinds of substrates (up to 89 \% ee for nitrodienes and up to 93 \% ee for β-nitrostyrene derivatives). Further transformation of the corresponding Friedel-Crafts alkylation product of indole with 2-propargyloxy-β- nitrostyrene was carried out to give the chiral isoxazolobenzoxepane derivative, which is of medicinal chemistry interest, with retained enantiomeric purity.",

keywords = "Alkenes, Alkylation, Asymmetric catalysis, Nitrogen heterocycles, Synthetic methods",

author = "Jiahuan Peng and Du, \{Da Ming\}",

year = "2012",

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doi = "10.1002/ejoc.201200382",

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T1 - Asymmetric Friedel-Crafts alkylation of indoles with nitrodienes and 2-propargyloxy-β-nitrostyrenes catalyzed by diphenylamine-linked bis(oxazoline)-Zn(OTf) 2 complexes

AU - Peng, Jiahuan

AU - Du, Da Ming

PY - 2012/7

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N2 - The catalytic asymmetric Friedel-Crafts reaction of indoles with nitrodienes and 2-propargyloxy-β-nitrostyrenes was systematically investigated with diphenylamine-linked bis(oxazoline)-Zn(OTf) 2 complexes. Moderate to good enantioselectivities were obtained with both kinds of substrates (up to 89 % ee for nitrodienes and up to 93 % ee for β-nitrostyrene derivatives). Further transformation of the corresponding Friedel-Crafts alkylation product of indole with 2-propargyloxy-β- nitrostyrene was carried out to give the chiral isoxazolobenzoxepane derivative, which is of medicinal chemistry interest, with retained enantiomeric purity.

AB - The catalytic asymmetric Friedel-Crafts reaction of indoles with nitrodienes and 2-propargyloxy-β-nitrostyrenes was systematically investigated with diphenylamine-linked bis(oxazoline)-Zn(OTf) 2 complexes. Moderate to good enantioselectivities were obtained with both kinds of substrates (up to 89 % ee for nitrodienes and up to 93 % ee for β-nitrostyrene derivatives). Further transformation of the corresponding Friedel-Crafts alkylation product of indole with 2-propargyloxy-β- nitrostyrene was carried out to give the chiral isoxazolobenzoxepane derivative, which is of medicinal chemistry interest, with retained enantiomeric purity.

KW - Alkenes

KW - Alkylation

KW - Asymmetric catalysis

KW - Nitrogen heterocycles

KW - Synthetic methods

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DO - 10.1002/ejoc.201200382

M3 - Article

AN - SCOPUS:84863897202

SN - 1434-193X

SP - 4042

EP - 4051

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

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ER -

Asymmetric Friedel-Crafts alkylation of indoles with nitrodienes and 2-propargyloxy-β-nitrostyrenes catalyzed by diphenylamine-linked bis(oxazoline)-Zn(OTf) ₂ complexes

Abstract

Keywords

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